Solid-phase synthesis of bleomycin A5 and three monosaccharide analogues: Exploring the role of the carbohydrate moiety in RNA cleavage

Craig J. Thomas, Alexander O. Chizhov, Christopher J. Leitheiser, Michael J. Rishel, Kazuhide Konishi, Zhi Fu Tao, Sidney Hecht

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The solid-phase synthesis of bleomycin A5 (BLM A5) and three monosaccharide analogues is presented. The monosaccharide analogues incorporated α-D-mannose, α-L-gulose, and α-L-rhamnose moieties in lieu of the disaccharide normally present in BLM A5. Also explored were the abilities of each of the monosaccharide congeners to cleave a 53-nt RNA. The elaboration of these carbohydrate-modified bleomycin analogues helps to define the role of the disaccharide moiety during the RNA cleavage event. The relatively facile solid-phase synthesis of bleomycin A5 and each of the carbohydrate analogues constitutes an important advance in the continuing mechanistic studies of bleomycin.

Original languageEnglish (US)
Pages (from-to)12926-12927
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number44
DOIs
StatePublished - Nov 6 2002
Externally publishedYes

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RNA Cleavage
Solid-Phase Synthesis Techniques
Monosaccharides
Carbohydrates
RNA
Disaccharides
Bleomycin
Rhamnose
Mannose
bleomycetin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Solid-phase synthesis of bleomycin A5 and three monosaccharide analogues : Exploring the role of the carbohydrate moiety in RNA cleavage. / Thomas, Craig J.; Chizhov, Alexander O.; Leitheiser, Christopher J.; Rishel, Michael J.; Konishi, Kazuhide; Tao, Zhi Fu; Hecht, Sidney.

In: Journal of the American Chemical Society, Vol. 124, No. 44, 06.11.2002, p. 12926-12927.

Research output: Contribution to journalArticle

Thomas, Craig J. ; Chizhov, Alexander O. ; Leitheiser, Christopher J. ; Rishel, Michael J. ; Konishi, Kazuhide ; Tao, Zhi Fu ; Hecht, Sidney. / Solid-phase synthesis of bleomycin A5 and three monosaccharide analogues : Exploring the role of the carbohydrate moiety in RNA cleavage. In: Journal of the American Chemical Society. 2002 ; Vol. 124, No. 44. pp. 12926-12927.
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